Patents by Inventor Paul S. Liu
Paul S. Liu has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 10464881Abstract: Disclosed is a process for preparing (Z)-endoxifen, comprising (i) recrystallizing an input crystalline solid comprising a mixture of (Z)-endoxifen (1) and (E)-endoxifen (2) from a first solvent to provide a first crystalline solid and a first mother liquor, wherein the first mother liquor has a ratio of (1) to (2) at least 1.3 times greater than the ratio in the input crystalline solid (1) and (2); (ii) recrystallizing a solid produced by concentrating the first mother liquor, or by removal of the first solvent from the first mother liquor, from a second solvent to give a second crystalline solid and a second mother liquor; (iii) optionally recrystallizing the second crystalline solid from the second solvent one to five additional times to give a third crystalline solid; wherein the third crystalline solid has a ratio of (Z)-endoxifen (1) to (E)-endoxifen (2) greater than 20:1.Type: GrantFiled: October 24, 2016Date of Patent: November 5, 2019Assignees: THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES, ALCHEM LABORATORIES CORPORATIONInventors: Paul S. Liu, Sergiy M. Denysenko, Guangfei Huang
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Publication number: 20180305295Abstract: Disclosed is a process for preparing (Z)-endoxifen, comprising (i) recrystallizing an input crystalline solid comprising a mixture of (Z)-endoxifen (1) and (E)-endoxifen (2) from a first solvent to provide a first crystalline solid and a first mother liquor, wherein the first mother liquor has a ratio of (1) to (2) at least 1.3 times greater than the ratio in the input crystalline solid (1) and (2); (ii) recrystallizing a solid produced by concentrating the first mother liquor, or by removal of the first solvent from the first mother liquor, from a second solvent to give a second crystalline solid and a second mother liquor; (iii) optionally recrystallizing the second crystalline solid from the second solvent one to five additional times to give a third crystalline solid; wherein the third crystalline solid has a ratio of (Z)-endoxifen (1) to (E)-endoxifen (2) greater than 20:1.Type: ApplicationFiled: October 24, 2016Publication date: October 25, 2018Inventors: Paul S. LIU, Sergiy M. DENYSENKO, Guangfei HUANG
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Patent number: 7834005Abstract: Disclosed are compounds of Formula I wherein X, Y, R1-R7, T1, T2, Z, and p are as described herein; a pharmaceutical composition comprising a compound of Formula I and a carrier; a method of inhibiting growth of a cell, which method comprises administering in an amount effective to inhibit growth a compound of Formula I; a method of treating cancer in a mammal, which method comprises administering in an amount effective to treat cancer a compound of Formula I; a method of treating a viral, parasitic, or bacterial infection of a cell, which method comprises administering in an amount effective to treat a viral, parasitic, or bacterial infection a compound of Formula I; and a method of preparing a compound of Formula I as described herein.Type: GrantFiled: February 13, 2009Date of Patent: November 16, 2010Assignees: The United States of America as represented by the Department of Health and Human Services, Starks Associates, Inc., Midwest Research Institute, Spirogen, Ltd.Inventors: Paul S. Liu, B. Rao Vishnuvajjala, Kenneth M. Snader, David E. Thurston, Philip W. Howard, Luke Y. Hsiao, Gregory Turner
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Publication number: 20090149449Abstract: Disclosed are compounds of Formula I wherein X, Y, R1-R7, T1, T2, Z, and p are as described herein; a pharmaceutical composition comprising a compound of Formula I and a carrier; a method of inhibiting growth of a cell, which method comprises administering in an amount effective to inhibit growth a compound of Formula I; a method of treating cancer in a mammal, which method comprises administering in an amount effective to treat cancer a compound of Formula I; a method of treating a viral, parasitic, or bacterial infection of a cell, which method comprises administering in an amount effective to treat a viral, parasitic, or bacterial infection a compound of Formula I; and a method of preparing a compound of Formula I as described herein.Type: ApplicationFiled: February 13, 2009Publication date: June 11, 2009Applicants: The United States of America, as represented by the Secretary, Dept. of Health and Human Service, Starks Associates, Inc., Midwest Research Institute, Spirogen, Ltd.Inventors: Paul S. Liu, B. Rao Vishnuvajjala, Kenneth M. Snader, David E. Thurston, Philip W. Howard, Luke Y. Hsiao, Gregory Turner
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Patent number: 7511032Abstract: Disclosed are compounds of Formula (I) wherein X, Y, Ri-R7, T1, T2, Z, and p are as described herein; a pharmaceutical composition comprising a compound of Formula (I) and a carrier; a method of inhibiting growth of a cell, which method comprises administering in an amount effective to inhibit growth a compound of Formula (I); a method of treating cancer in a mammal, which method comprises administering in an amount effective to treat cancer a compound of Formula (I); a method of treating a viral, parasitic, or bacterial infection of a cell, which method comprises administering in an amount effective to treat a viral, parasitic, or bacterial infection a compound of Formula (I); and a method of preparing a compound of Formula (I) as described herein.Type: GrantFiled: October 22, 2004Date of Patent: March 31, 2009Assignees: The United States of America as represented by the Secretary, Department of Health and Human Services, Starks Associates, Inc., Midwest Research Institute, Spirogen, Ltd.Inventors: Paul S Liu, B. Rao Vishnuvajjala, Kenneth M Snader, David E Thurston, Philip W Howard, Luke Y Hsiao, Gregory Turner
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Patent number: 7244724Abstract: A compound of formula I: or solvate thereof, wherein n is 1 to 10, and M and M? are independently selected from monovalent pharmaceutically acceptable cations, or together represent a divalent pharmaceutically acceptable cation.Type: GrantFiled: May 13, 2005Date of Patent: July 17, 2007Assignees: United States of America, Represented by the Secretary, Department of Health and Human Services, Spirogen, Ltd.Inventors: Paul S. Liu, B. Rao Vishnuvajjala, Kenneth M. Snader, David E. Thurston, Philip Howard, Stephen Gregson
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Patent number: 6136820Abstract: A method for inhibiting the formation of glucose by the administration of castanospermine is described herein. In addition, a new process for the isolation of castanospermine from Castanospermum australe is also described.Type: GrantFiled: December 5, 1990Date of Patent: October 24, 2000Assignee: Merrell Pharmaceuticals Inc.Inventors: Paul S. Liu, Barry L. Rhinehart
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Patent number: 5385911Abstract: Certain Castanospermine ester derivatives of the formula: ##STR1## wherein R, R.sub.1 and R.sub.2 are each independently hydrogen, C.sub.1-14 alkanoyl, C.sub.1-14 alkenoyl, cyclohexanecarbonyl, C.sub.1-8 alkoxyacetyl, ##STR2## naphthalenecarbonyl optionally substituted by methyl or halogen; phenyl (C.sub.2-6 alkanoyl) wherein the phenyl is optionally substituted by methyl or halogen; cinnamoyl; pyridinecarbonyl optionally substituted by methyl or halogen; dihydropyridine carbonyl optionally substituted by C.sub.1 -C.sub.10 alkyl; thiophenecarbonyl optionally substituted by methyl or halogen; or furancarbonyl optionally substituted by methyl or halogen; Y is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen, trifluoromethyl, C.sub.1-4 alkylsulfonyl, C.sub.1-4 alkylmercapto, cyano or dimethylamino; Y' is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen or it is combined with Y to give 3,4-methylenedioxy; Y" is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or halogen; with R, R.sub.1 and R.sub.Type: GrantFiled: April 1, 1993Date of Patent: January 31, 1995Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Sai P. Sunkara, Paul S. Liu, A. Stanley Tyms, Debra L. Taylor
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Patent number: 5079254Abstract: Amide and ester derivatives of 6-amino-octahydro-1,7,8-indolizinetriol are described herein. The compounds are prepared from castanospermine by replacing the appropriate hydroxy function with an amino function while protecting the other hydroxy groups in the meantime. The compounds are useful as hexosaminidase inhibitors.Type: GrantFiled: June 4, 1990Date of Patent: January 7, 1992Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Paul S. Liu, Mohinder S. Kang
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Patent number: 5028614Abstract: The present invention describes a group of polyhydroxylated indolizidines and quinolizidines and their esters. These compounds are prepared starting from 2,6-dideoxy-2,6-dideoxy-2,6-imino-1,3,4,5-tetrakis-O- (phenylmethyl)-D-glycero-L-gulo-heptitol or a corresponding N-substituted compound. The compounds are useful in the treatment of diabetes and as .alpha.-glucosidase I inhibitors.Type: GrantFiled: March 30, 1990Date of Patent: July 2, 1991Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Paul S. Liu, Mohinder S. Kang, Roland S. Rogers, Barry L. Rhinehart
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Patent number: 5017563Abstract: Castanospermine mono- and di-esters and glycosides active as inhibitors of carbohydrate digestive enzymes and useful in treating diabetes are described herein. The compounds are prepared by the reaction of castanospermine with an appropriate acid halide or anhydride or with an appropriate glycosyl halide or glycosyl acetimidate under conditions which would favor the isolation of the mono- and di-esterified and glycosylated products. Various blocking groups, which can be selectively removed under mild conditions, can also be used to favor the formation of certain isomers.Type: GrantFiled: May 1, 1990Date of Patent: May 21, 1991Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Paul S. Liu, Barry L. Rhinehart, John K. Daniel
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Patent number: 5004746Abstract: Certain Castanospermine ester derivatives are disclosed to be effective in treating retroviral infections including HIV infections and are thus useful in the treatment of AIDS and ARC.Type: GrantFiled: September 29, 1987Date of Patent: April 2, 1991Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Paul S. Liu, Sai P. Sunkara, Terry L. Bowlin
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Patent number: 4952585Abstract: A method for the inhibition of tumor metastases is described herein. The method makes use of the administration of certain castanospermine esters or their pharmaceutically acceptable salts.Type: GrantFiled: December 15, 1988Date of Patent: August 28, 1990Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Sai P. Sunkara, Paul S. Liu
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Patent number: 4880917Abstract: A procedure for the mild conversion of a carbonitrile to the corresponding carboxylic acid by first using trifluoroacetic acid in the presence of a catalytic amount of mercuric ion followed by oxidative hydrolysis with dinitrogen tetroxide is described herein. The use of this procedure in the preparation of 1,3,4,5-tetra-O-benzoyl-2,6-dideoxy-2,6-imino-D-glycero-L-gulo-heptitol hydrochloride is also described here.Type: GrantFiled: July 1, 1988Date of Patent: November 14, 1989Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Peter B. Anzeveno, John K. Daniel, Laura J. Creemer, Paul S. Liu
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Patent number: 4792558Abstract: A method for the inhibition of tumor metastases is described herein. The method makes use of the administration of castanospermine.Type: GrantFiled: May 29, 1987Date of Patent: December 20, 1988Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Sai P. Sunkara, Barry L. Rhinehart, Paul S. Liu
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Patent number: 4634765Abstract: Homonojirimycin glycosides active as inhibitors of carbohydrate digestive enzymes are described herein. The compounds are prepared by the reaction of an appropriately protected homonojirimycin with a protected glycosyl halide followed by removal of the protecting groups.Type: GrantFiled: December 18, 1984Date of Patent: January 6, 1987Assignee: Merrell Dow Pharmaceuticals Inc.Inventor: Paul S. Liu
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Patent number: 4275057Abstract: Seven-membered heterocyclic nucleosides used to inhibit the deamination enzyme responsible for the inactivation of arabinosylcytosine (ara--C). Preferred nucleosides containing a seven-member aglycone are as follows: ##STR1## Preferred aglycones are as follows: ##STR2## Active components utilized against pyrimidine deaminases from mammalian tissues (mouse kidney and human liver) showed optimum advantage when compared with tetrahydrouridine (THU).Type: GrantFiled: January 28, 1980Date of Patent: June 23, 1981Assignee: The United States of America as represented by the Department of Health, Education and WelfareInventors: Victor E. Marquez, Paul S. Liu, John S. Driscoll